Chicago is a cold place to be in January. Much more unpleasant than San Francisco. I should know – I flew from San Francisco to Chicago three times. In one weekend. And I did that three weekends in a row. I only made it out of Chicago O’Hare Airport on one of those nine trips, but each time I stepped off the plane, the bitter chill that blasted its way through the gap between the jet bridge and Boeing 767 metal was an unmistakable welcome to Chicago.

But I’m guessing you don’t want to hear about the weather in Chicago. You want to know why I made nine round-trips across the country over the course of six days. It wasn’t for business and it wasn’t for a girl (sadly). If you think about it for a moment, there’s only one thing it could really be for.

In December, I was browsing some blogs trying to figure out a way to use a bunch of Avios points that I had received from a British Airways credit card promotion. One of those blogs, “One Mile at a Time” was run by a guy going by the handle of Lucky, and in one post he was raving about a couple of promotions that American Airlines was running. The combination of those promotions made it possible to go from having no status with American all the way up to its top tier frequent flyer status – Executive Platinum – in the space of three weekends and for under $2,000. You had to live in California, Texas or Illinois to be able to take advantage of the opportunity. It caught my eye.

Achieving Executive Platinum status ordinarily requires you to fly 100,000 miles. That’s over 160,000 kilometres, or seven roundtrips between San Francisco and Sydney, or about 200 hours of flying.

“Lucky” is Ben Schlappig. He flies an average of about 300,000 miles a year, most of it in business and first class. He spends almost a third of the year in four and five star hotels. He has top-tier status with most, if not all, U.S. airlines. And Ben is, like, 21 years old. He just graduated from college last May.

Ben is a hardcore mileage runner. This means he often takes flights for the sole purpose of flying, and not to go somewhere in particular. Although most would think this is a highly peculiar hobby, as he mentioned in an interview, his classmates spent their weekends getting plastered at the bar, while he spent his weekends criss-crossing the country on cheap flights racking up frequent flyer miles. This, combined with savvy management of credit card point promotions, and a whole lot of tricks he picked up from his experiences, meant that he was soon regularly flying in first and having encounters with celebrities and politicians (on a recent international flight, he shared the cabin with Grace Mugabe – yes, the Zimbabwean President’s wife, whom he commented on with scorn). From what I can gather, Ben does not come from money – mileage running is all about getting great bargains, so he appears to have managed this all on a college student’s income. He now runs a side business helping people find ways to redeem their frequent flyer points (if you can’t find seat availability, for $150 a redemption, he’ll find some creative routings for you to make it work).

On his blog, Ben explained that American was running a promotion which doubled “elite qualifying miles” (EQM) for all of their flights in January. American was running a second promotion with doubled EQM for all flights between LAX/SFO (Los Angeles and San Francisco) and DFW/ORD (Dallas-Fort Worth and Chicago O’Hare). A customer service rep had confirmed that these two promotions were stackable. Furthermore, American was offering discounted flights between SFO-ORD for only $200 return (plus about $20 in tax) throughout January. The sentiment was that American, which had just entered Chapter 11 bankruptcy protection, was doing this to attract more customers which would help it to fight its way out of its financial woes. In a nutshell, one return flight to Chicago would net over 10,000 miles.

I stopped telling my friends what I was doing after I got horrified reactions from a couple of them who thought I had quite frankly lost my marbles, or decided to invest in some Ponzi scheme. Why on earth would anyone in their right mind want to put themselves through what I was putting myself through?

I was never actually asked, “If this is such a good deal, then why isn’t anyone else doing it?” But the answer to that question is: “there were.”

If you look hard enough, you’ll find that almost every enthusiast community has a bustling online web forum which acts as a sort of global clearinghouse for information about it. Like sci-fi and fantasy? You’ll find your ilk on StarDestroyer.net. If BMWs are your thing, you’ll find enthusiasts on bimmerpost.com (who sign their messages with the list of BMWs they’ve owned in the past). If you think quantitative easing is going to inflate the value out of the US dollar and like to keep your assets in gold and silver bullion, Silver Stackers is your go-to place. Aircraft and aviation? Airliners.net. And for frequent flyers, there’s the venerable FlyerTalk forums.

The folk at FlyerTalk (or FT) had cottoned on to this AA promotion-fest a while ago and a couple hundred people had not only said they were going to take advantage of it, but they had all submitted their complete flight itineraries for January, and a forum member named “2millionquest” was diligently compiling all that data.

I met some of these people at the airport. I won’t lie, it was surreal stumbling off the plane from San Francisco, only to walk a few metres to the next gate and fly straight back there. The only thing more surreal was that when I was waiting to board the return flight, I’d recognize anywhere from two to ten familiar faces – people who had just got off the same flight I had, and who were now heading back to San Francisco. Upgrade request lists on some flights were 30-deep (that’s about three to four times what you’d normally see) because a lot of elite status members were partaking in these MRs in a bid to renew their status.

After a round-trip, it’s pretty obvious who is embarking on the same escapade, so people would just walk up to each other and say, “Hey, are you on FT?” or “You mileage running?” And then, “Wanna hit the AC?” It was like some sort of secret handshake. (AC stands for Admiral’s Club – the brand name for American’s airport lounges.)

The mileage runners (MRs) tended to congregate in airline lounges, away from the hoi polloi milling around the departure gates. Many MRs didn’t have lounge access, so people were messaging other MRs through FT and requesting to be “guested in.”

I reached out to one FT member who was taking the same Saturday night red eye out of SFO and he gave me his mobile number. I texted him when I was outside the AA lounge and he came out to meet me. He was a tall, congenial Asian guy called Allen. Pretty much all we talked about was mileage running. It was a fascinating conversation. The only personal details I got out of him was that he was a hardware engineer from Sunnyvale in his early 30s, having graduated from MIT about 10 years ago. After a few words about how software engineering was where all the money was these days in the Valley, he told me how he had been mileage running for about a year now. He asked if I had any good MR stories to share, and I confessed I was a complete newbie to the game.

I asked him whether the promotion we were currently taking advantage of was a frequent occurrence and he said that a deal this good only happened maybe once every 5-10 years. He mentioned that he had picked up a lot of information from FT, and also from a seminar that a few "luminaries" in the FT community had run in Chicago a few months earlier. I learned about "fuel dumps", how best to use Avios points, why spending $450 for an Amex Platinum card might actually be a good deal, and a bunch of other random tips. After a while, we decided to go hunting around looking for other FTs. They weren’t hard to spot. Most lounge guests were either alone or grouped in twos and threes. But in one corner, a group of about a half dozen mismatched people were engaged in lively conversation.

I had walked into a den of pretty serious MRs. They were mostly a generation older than me, and mostly men (there were two women). The discussion was all about flying, and I think there was a measure of shared relief among the group that they could freely talk about mileage running with other like-minded individuals without worrying they’d get the same shocked looks that I was getting from my friends. Acronyms sprayed the air like machine gun fire. And from what I could tell, it had been a long time since some of them had flown in economy.

One lady, who was from Sacramento, recounted a story about how she had to travel to London via New York and freaked out when she couldn’t get an upgrade out of coach. “There was no way I was flying international at the back of the plane,” she snorted, and then told us how she rerouted the flight through two different cities and managed to get the upgrade.

A hardened, older gentleman with a pot belly and sandals was showing off his itinerary, which he had done up in an Excel spreadsheet in meticulous detail. He was flying 11 segments that weekend.

Another lady told the group how she had discovered which lounge in DFW had the best showers. “They have nozzles coming at you from the sides as well as above!”

Then there was a guy called Ben (not the same Ben). Ben was based in Dallas and he was already an Executive Platinum member (or “Exec Plat” as they called it). He had heard a rumor that American was going to either lift the mileage thresholds or add additional tiers, and he was generating more miles “just in case”. Just in case. “No offence,” he said to the group, “but a lot of people don’t see why an Exec Plat who has flown 100k miles should be treated the same as one who has flown 200k miles.” Ben was a middle-aged tech manager who flew to Tokyo several times each quarter (I’m guessing he was an EDS exec). In doing so, he had racked up 6.5 million miles with American (most of them “butt-in-seat” miles). If you’re now thinking of the movie “Up In The Air,” you’re not the only one. If you haven’t seen it, George Clooney plays a frequently flying businessman who hits an insane number of miles flying American.

Sitting in on that group’s conversation was scary. It’s like any conversation where everyone else is well-informed and super passionate about some niche topic and you’re not. I might as well have walked into a medical conference. Mileage running has its own glossary, and these people knew an incredible amount about the art form. About the planes, the airports, the airlines, the frequent flyer programs, the credit cards, the hotels, the best ways to redeem points, the best way to get upgrades, the best ways to route flights, the best way to find MRs, the best way to talk to gate agents. There were so many facets to navigating the air travel industry. I was lost and I had nothing to contribute except questions.

Allen and I arrived at the gate just as a final call was being made for our names. We were traveling light (just a laptop bag for me), so we were able to make our way straight to our seats without having to wait in the aisle for people to hoist bags into overhead bins and jostle infants into seats. When we arrived in Chicago, we went straight to the AA lounge to wait for our next flight. Allen pulled out his laptop and gave me a tour of ExpertFlyer, a subscription website which people use to discover mileage runs, track fares, and check award seat availability. “If I wanted to use my miles to book a flight in F [first class] to Hong Kong tonight, I could do it. Look, there’s three spots available,” he said, jabbing at the screen.

Spending all that time up in the air was no where near as bad as it sounds. Each weekend was more or less the same routine. I’d drive to SFO on Friday night and park at an off-site lot using a discount coupon. I’d hop on a red-eye to ORD, then return to SFO by mid-morning. I’d have the rest of Saturday to myself, before driving back to SFO at night. Then it’d be another red-eye, returning to SFO by mid-morning again. I’d then head straight back out to ORD and catch the final evening flight back to SFO. Due to ticket availability, I had to route through Dallas a couple of times.

SFO to ORD is only about 4 hours, so it’s not exactly a long-haul flight. Almost all the flights had wifi, so I could do some work and surf the net. (Incidentally, if you want to see why Apple’s stock price hit $500, you only have to walk around the cabin – anyone who is on an electronic device is on a iPhone, iPad or Macbook, with the occasional Kindle.) The flight attendants brought drinks around and I listened to music on some noise-cancelling headphones. The Economist gets delivered to me on Fridays, so I had the chance to read it cover to cover over the weekend during the periods where electronics have to be turned off in flight.

And, I actually like planes and airports – with the exception of security screening checkpoints. I like watching massive people carriers maneuver around taxiways and roar off into the sky. I like the bustle of airports, where people from all over the country and the world mix together. I like gazing out the window at the changing landscape – the rolling hills of the Bay Area, the cornfields of the flyover states, snow-covered mountain ranges, and the frigid vistas of the north-eastern states (so much more interesting than flying across Australia, which is just unending stretches of desert).

In between flights, I could stretch my legs and wander around the terminal. I got to know where everything was – where to get food, power, and where to sit and wait. American flies out of a newly refurbished Terminal 2 at SFO, and it’s a surprisingly pleasant place to be.

I would even say it was relaxing, actually.

Not everything was smooth. It was, after all, the middle of winter. The rainy season at SFO and the snowy season at ORD constantly threatened to disrupt travel. In January 2010, freak snowstorms in the U.S. threw air travel into chaos. If even one of my flights was cancelled (much less a repeat of 2010), I would have fallen short of 100k miles. You generally aren’t entitled to earn miles for flights you don’t actually physically board. Luckily, the weather held up for the most part. Before the second weekend, a cold front moved into Chicago on Friday, dumping 8 inches of snow and causing the cancellation of about 50% of flights into ORD. The forums were abuzz with people trying to figure out how they could claim "ORC" or original routing credit for the flights they no longer were able to take (apparently Customer Relations, and not Customer Support is the department you want to contact for these kinds of discretionary requests). The storm had moved on by the time my flight arrived on early Saturday morning.

Three of my flights had “mechanicals” which caused delays, but nothing too disruptive.

Only one of my flights had a real issue. My final flight from ORD to SFO during the second weekend was delayed. It was snowing in Chicago, but it was the fog in San Francisco that caused at first a one hour delay, then a two hour delay, and then a three hour delay. The 49ers were playing the Giants for a berth in the Superbowl that evening, so at least the delay meant that I had the opportunity to watch the whole game. The flight was heading back to SFO, which meant a lot of 49ers fans were at the gate watching as well. Unfortunately, they lost in overtime. When we eventually boarded the plane, it had a “mechanical.” Something to do with the fuel pump. So we had to wait another hour for 16 volunteers to deplane and for their luggage to be unloaded. I ended up getting home at about 2.00am that night.

So, what did I get for all my troubles?

After the first week, I got upgraded to Gold. Being able to bypass the long security lines was nice. The front seats and exit rows in the economy cabin (so called “preferred seating”) were also now available for me to book. After the second week, I moved up to Platinum. It was nice being able to board the plane early. When I went to the gate agent to get a boarding pass, she noted that I had a middle seat and, without me even asking, she said she’d move me to my preferred windows seat up the front of the cabin. One of my upgrades to first class also cleared.

When I hit Executive Platinum, I became entitled to unlimited complimentary domestic upgrades. But the real money is the 8 “systemwide upgrades” that Exec Plat members are given each year. SWUs allow you to upgrade to the next class of service on any American-operated flight (very handy for international trips, and if you don’t use them all, you can gift them to friends and family). You also get extra luggage allowance. You get to board the plane first, your luggage comes out first, and because it qualifies you for OneWorld Emerald status, you get to use the first class lounges of OneWorld airlines throughout the world. Telephone booking fees are waived. So now, to make use of the time and money I invested in this, I just have to get flying… but not to Chicago!

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